Compound, coating composition comprising same, and organic light-emitting device

ABSTRACT

The present specification relates to a compound, a coating composition including the same, and an organic light emitting device.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a national phase entry under 35 U.S.C. § 371 ofInternational Application No. PCT/KR2019/006206 filed May 23, 2019,which claims priority from Korean Patent Application No. 10-2018-0058329filed May 23, 2018, all of which are incorporated herein by reference.

TECHNICAL FIELD

The present specification relates to a compound, a coating compositionincluding the same, and an organic light emitting device.

BACKGROUND ART

An organic light emission phenomenon is one of examples converting acurrent to visible light by an internal process of specific organicmolecules. A principle of an organic light emission phenomenon is asfollows. When an organic material layer is placed between an anode and acathode and a current is applied between the two electrodes, electronsand holes are injected to the organic material layer from the cathodeand the anode, respectively. The holes and the electrons injected to theorganic material layer recombine to form excitons, and light emits whenthese excitons fall back to the ground state. An organicelectroluminescent device using such a principle may be generally formedwith a cathode, an anode, and an organic material layer placedtherebetween, for example, an organic material layer including a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer and an electron injection layer.

Materials used in an organic light emitting device are mostly pureorganic materials or complex compounds in which organic materials andmetals form complexes, and may be divided into hole injection materials,hole transfer materials, light emitting materials, electron transfermaterials, electron injection materials and the like depending on theapplication. Herein, as the hole injection material or the hole transfermaterial, organic materials having a p-type property, that is, organicmaterials readily oxidized and having an electrochemically stable statewhen oxidized, are generally used. Meanwhile, as the electron injectionmaterial or the electron transfer material, organic materials having ann-type property, that is, organic materials readily reduced and havingan electrochemically stable state when reduced, are generally used. Asthe light emitting material, materials having both a p-type property andan n-type property, that is, materials having a stable form in bothoxidized and reduced states, are preferred, and materials having highlight emission efficiency converting, when excitons are formed, theexcitons to light are preferred.

In addition to the properties described above, it is preferred thatmaterials used in an organic light emitting device additionally haveproperties as follows.

First, materials used in an organic light emitting device preferablyhave excellent thermal stability. This is due to joule heat produced bycharge migration in the organic light emitting device. NPB (n-propylbromide) normally used as a hole transfer layer material currently has aglass transition temperature of 100° C. or lower, and has a problem inthat it is difficult to use in organic light emitting devices requiringa high current.

Second, in order to obtain a highly efficient organic light emittingdevice capable of low voltage driving, holes or electrons injected intothe organic light emitting device need to be smoothly transferred to alight emitting layer, and at the same time, the injected holes andelectrons need to be kept from escaping out of the light emitting layer.For this, materials used in the organic light emitting device need tohave a proper band gap and a HOMO or LUMO energy level.Poly(3,4-ethylenedioxythiophene) doped with poly(styrenesulfonic acid)(PEDOT:PSS) currently used as a hole transfer material in an organiclight emitting device manufactured using a solution coating method has alower LUMO energy level compared to a LUMO energy level of organicmaterials used as a light emitting layer material, and therefore, has aproblem in manufacturing an organic light emitting device with highefficiency and long lifetime.

In addition thereto, materials used in an organic light emitting deviceneed to have excellent chemical stability, charge mobility, andinterface property with electrodes or adjacent layers. In other words,materials used in an organic light emitting device need to undergo lessmaterial deformation caused by moisture or oxygen. In addition, byhaving proper hole or electron mobility, the materials need to maximizeexciton formation through balancing hole and electron density in a lightemitting layer of the organic light emitting device. For devicestability, the materials also need to improve an interface withelectrodes including metals or metal oxides.

Accordingly, development of organic materials fulfilling suchrequirements has been required in the art.

DISCLOSURE Technical Problem

The present specification is directed to providing a compound, a coatingcomposition including the same, and an organic light emitting device.

Technical Solution

One embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1.

In Chemical Formula 1,

Ar1 and Ar2 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group,

R1 to R4 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heterocyclic group,

r1 to r3 are each from 1 to 3,

r4 is from 1 to 4,

when r1 to r4 are each 2 or greater, the two or more R1 to R4 are eachthe same as or different from each other,

X1 and X2 are the same as or different from each other, and eachindependently

each

means a linking site,

a1 is 0 or 1, and a2 is an integer of 0 to 2,

when a2 is 0, L2 is a substituted or unsubstituted aryl group; or asubstituted or unsubstituted aralkyl group,

when a2 is 1, L2 is a direct bond; or a substituted or unsubstitutedarylene group,

when a2 is 2, L2 is a trivalent substituted or unsubstituted aryl group,

L1 is a substituted or unsubstituted arylene group,

m is an integer of 1 or 2, and when m is 2, L1s are the same as ordifferent from each other,

n is an integer of 1 or 2, and when n is 1, L3 is a substituted orunsubstituted arylene group, and when n is 2, L3s are each a substitutedor unsubstituted arylene group and a substituted or unsubstitutedalkylene group, and

0≤a1+a2≤2.

Another embodiment of the present specification provides a coatingcomposition including the compound.

Another embodiment of the present specification provides an organiclight emitting device including a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layersinclude the coating composition and a cured material thereof.

Advantageous Effects

An organic material layer formed using a compound according to oneembodiment of the present specification has excellent thermal andphotostability after being cured through heat and light, and does nothave solubility for other solvents, and therefore, a laminationfilm-forming process can be performed on the formed film through anothersolution process.

In addition, a compound according to one embodiment of the presentspecification is used as a material of an organic material layer of anorganic light emitting device, and is capable of lowering a drivingvoltage of the organic light emitting device.

In addition, a compound according to one embodiment of the presentspecification is used as a material of an organic material layer of anorganic light emitting device, and is capable of enhancing lightefficiency.

In addition, a compound according to one embodiment of the presentspecification is used as a material of an organic material layer of anorganic light emitting device, and is capable of enhancing lifetimeproperties of the device.

In addition, a compound according to the present specification has highsolubility for an organic solvent, and therefore, a solution process canbe used, and as a result, large area devices can be manufactured, andthe compound can be used as a material of an organic material layer ofan organic light emitting device.

DESCRIPTION OF DRAWINGS

The FIGURE is a diagram illustrating an example of an organic lightemitting device according to one embodiment of the presentspecification.

REFERENCE NUMERAL

-   -   101: Substrate    -   201: Anode    -   301: Hole Injection Layer    -   401: Hole Transfer Layer    -   501: Light Emitting Layer    -   601: Electron Injection and Transfer Layer    -   701: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides a compoundrepresented by Chemical Formula 1.

The structure of the compound represented by Chemical Formula 1according to the present specification includes a curing group that iscurable, which has an advantage in that, when film-forming other layerssuch as a hole transfer layer or a light emitting layer on the top of anorganic material layer formed with a coating composition including thesame and a cured material thereof, various solvents may be usedregardless of the solvent. In addition, the compound of Chemical Formula1 has an advantage of efficiently injecting and transferring holes byhaving electron-sufficient arylamine group and fluorene group. Inaddition, the compound of Chemical Formula 1 has a dipole moment causedfrom an asymmetric molecular structure making efficient hole transferpossible, and high solubility obtained therefrom has an advantage inthat various solvents may be used in a solution process.

Examples of substituents in the present specification are describedbelow, however, the substituents are not limited thereto.

In the present specification,

means a linking site.

The term “substitution” means a hydrogen atom bonding to a carbon atomof a compound is changed to another substituent. The position ofsubstitution is not limited as long as it is a position at which thehydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

The term “substituted or unsubstituted” in the present specificationmeans being substituted with one, two or more substituents selected fromthe group consisting of deuterium; a halogen group; a nitrile group; analkyl group; a fluoroalkyl group; a cycloalkyl group; an alkoxy group;an aryloxy group; an aralkyl group; an aryl group; and a heteroarylgroup including one or more of N, O, S, Se and Si atoms, beingsubstituted with a substituent linking two or more substituents amongthe substituents illustrated above, or having no substituents.

In the present specification, the alkyl group may be linear or branched,and although not particularly limited thereto, the number of carbonatoms is preferably from 1 to 50 and more preferably from 1 to 30.Specific examples thereof may include methyl, ethyl, propyl, n-propyl,isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl,1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl,tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl,1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl,tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl,2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl,4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, the fluoroalkyl group is not particularlylimited, but preferably has 1 to 5 carbon atoms and more preferably 1 to3 carbon atoms. Specific examples thereof may include a trifluoromethylgroup, a pentafluoroethyl group and the like, but are not limitedthereto.

In the present specification, the cycloalkyl group is not particularlylimited, but preferably has 3 to 60 carbon atoms, and more preferablyhas 3 to 30 carbon atoms. Specific examples thereof may includecyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl,2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl,4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl,4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but arenot limited thereto.

In the present specification, the alkoxy group may be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but is preferably from 1 to 30. Specific examplesthereof may include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy,n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and thelike, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group, anarylthioxy group, an arylsulfoxy group, an N-arylalkylamine group, anN-arylheteroarylamine group and an arylphosphine group is the same asthe examples of the aryl group described above. Specific examples of thearyloxy group may include a phenoxy group, a p-tolyloxy group, anm-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxygroup, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxygroup and the like, examples of the arylthioxy group may include aphenylthioxy group, a 2-methylphenylthioxy group, a4-tert-butylphenylthioxy group and the like, and examples of thearylsulfoxy group may include a benzenesulfoxy group, a p-toluenesulfoxygroup and the like, but are not limited thereto.

In the present specification, the aralkyl group means an alkyl groupsubstituted with an aryl group, and although not particularly limitedthereto, the aralkyl group preferably has 7 to 30 carbon atoms. Specificexamples thereof may include a benzyl group, a phenethyl group, aphenyloctyl group, a phenylhexyl group and the like, but are not limitedthereto.

When the aryl group is a monocyclic aryl group in the presentspecification, the number of carbon atoms is not particularly limited,but is preferably from 6 to 50 and more preferably from 6 to 30.Specific examples of the monocyclic aryl group may include a phenylgroup, a biphenyl group, a terphenyl group, a quaterphenyl group and thelike, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbonatoms is not particularly limited, but is preferably from 10 to 50 andmore preferably from 10 to 30. Specific examples of the polycyclic arylgroup may include a naphthyl group, an anthracenyl group, a phenanthrylgroup, a pyrenyl group, a perylenyl group, a triphenyl group, achrysenyl group, a fluorenyl group and the like, but are not limitedthereto.

In the present specification, the heterocyclic group includes one ormore of N, O, S, Si and Se as a heteroatom, and although notparticularly limited thereto, the number of carbon atoms is preferablyfrom 2 to 60 and more preferably from 2 to 30. Examples of theheterocyclic group may include a thiophene group, a furan group, apyrrole group, an imidazole group, a thiazole group, an oxazole group,an oxadiazole group, a triazole group, a pyridine group, a bipyridinegroup, a pyrimidine group, a triazine group, an acridine group, apyridazine group, a pyrazine group, a quinoline group, a quinazolinegroup, a quinoxaline group, a phthalazine group, a pteridine group, apyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazinegroup, an isoquinoline group, an indole group, a pyrido indole group,5H-indeno pyrimidine, a carbazole group, a benzoxazole group, abenzimidazole group, a benzothiazole group, a benzocarbazole group, abenzothiophene group, a dibenzothiophene group, a benzofuran group, adibenzofuran group, a phenanthroline group, a thiazolyl group, anisoxazolyl group, an oxadiazolyl group, a thiadiazolyl group and thelike, but are not limited thereto.

In the present specification, the heteroaryl group may be selected fromamong the examples of the heterocyclic group except for those that arearomatic, but is not limited thereto.

In the present specification, the alkylene group means an alkyl grouphaving two bonding sites, that is, a divalent group. Descriptions on thealkyl group provided above may be applied thereto except for those thatare each divalent.

In the present specification, the arylene group means an aryl grouphaving two bonding sites, that is, a divalent group. Descriptions on thearyl group provided above may be applied thereto except for those thatare each divalent.

In the present specification, the heteroarylene group means a heteroarylgroup having two bonding sites, that is, a divalent group. Descriptionson the heteroaryl group provided above may be applied thereto except forthose that are each divalent.

In one embodiment of the present specification, Ar1 and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup.

In one embodiment of the present specification, Ar1 and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted aryl group having 6 to 30 carbon atoms; or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted aryl group having 6 to 20 carbon atoms; or a substitutedor unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted naphthyl group; a substituted orunsubstituted phenanthrene group; a substituted or unsubstitutedfluorene group; a substituted or unsubstituted spirobifluorene group; ora substituted or unsubstituted dibenzofuran group.

In one embodiment of the present specification, Ar1 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted naphthyl group; a substituted orunsubstituted phenanthrene group; a substituted or unsubstitutedfluorene group; a substituted or unsubstituted spirobifluorene group; ora substituted or unsubstituted dibenzofuran group.

In one embodiment of the present specification, Ar1 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted naphthyl group; a substituted orunsubstituted phenanthrene group; a substituted or unsubstitutedfluorene group; a substituted or unsubstituted spirobifluorene group; ora substituted or unsubstituted dibenzofuran group, and in the definitionof Ar1, the “substituted or unsubstituted” means being unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of deuterium, a halogen group, a fluoroalkyl group, an alkylgroup, an aralkyl group, an aryloxy group and an aryl group.

In one embodiment of the present specification, Ar1 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted naphthyl group; a substituted orunsubstituted phenanthrene group; a substituted or unsubstitutedfluorene group; a substituted or unsubstituted spirobifluorene group; ora substituted or unsubstituted dibenzofuran group, and in the definitionof Ar1, the “substituted or unsubstituted” means being unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of deuterium, F, a trifluoromethyl group, a methyl group, abutyl group, a phenylpropanyl group, an ethylhexyloxy group, a hexylgroup, an octyl group, a decyl group and a phenyl group.

In one embodiment of the present specification, Ar2 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar2 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; or a substituted or unsubstituted naphthyl group, and in thedefinition of Ar2, the “substituted or unsubstituted” means beingunsubstituted or substituted with one or more substituents selected fromthe group consisting of deuterium, an alkyl group, an alkoxy group andan aryloxy group.

In one embodiment of the present specification, Ar2 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; or a substituted or unsubstituted naphthyl group, and in thedefinition of Ar2, the “substituted or unsubstituted” means beingunsubstituted or substituted with one or more substituents selected fromthe group consisting of deuterium, a methyl group, a butyl group, anethylhexyloxy group and a phenoxy group.

In one embodiment of the present specification, R1 to R4 are the same asor different from each other, and each independently hydrogen;deuterium; a halogen group; a nitrile group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted aryl group; ora substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, r1 to r3 are each from 1to 3, r4 is from 1 to 4, and when r1 to r4 are each 2 or greater, thetwo or more R1 to R4 are each the same as or different from each other.

In one embodiment of the present specification, R1 to R4 are hydrogen.

In one embodiment of the present specification, X1 and X2 are the sameas or different from each other, and each independently

In one embodiment of the present specification, a1 is 0 or 1, and a2 isan integer of 0 to 2.

In one embodiment of the present specification, when a2 is 0, L2 is asubstituted or unsubstituted aryl group; or a substituted orunsubstituted aralkyl group.

In one embodiment of the present specification, when a2 is 0, L2 is asubstituted or unsubstituted aryl group; or an aralkyl group.

In one embodiment of the present specification, when a2 is 0, L2 is aphenyl group unsubstituted or substituted with deuterium, a halogengroup, an alkyl group or an alkoxy group; a fluorene group unsubstitutedor substituted with deuterium, a halogen group, an alkyl group or analkoxy group; or a benzyl group unsubstituted or substituted withdeuterium, a halogen group, an alkyl group or an alkoxy group.

In one embodiment of the present specification, when a2 is 1, L2 is adirect bond; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, when a2 is 1, L2 is adirect bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, when a2 is 1, L2 is adirect bond; or a phenylene group.

In one embodiment of the present specification, when a2 is 2, L2 is atrivalent substituted or unsubstituted aryl group.

In one embodiment of the present specification, when a2 is 2, L2 is atrivalent substituted or unsubstituted phenyl group.

In one embodiment of the present specification, L1 and L3 are the sameas or different from each other, and each independently a substituted orunsubstituted arylene group.

In one embodiment of the present specification, L1 and L3 are the sameas or different from each other, and each independently a substituted orunsubstituted phenylene group.

In one embodiment of the present specification, L1 is a substituted orunsubstituted phenylene group; a substituted or unsubstitutednaphthylene group; or a substituted or unsubstituted divalent fluorenegroup.

In one embodiment of the present specification, L1 is a substituted orunsubstituted phenylene group; or a substituted or unsubstituteddivalent fluorene group.

In one embodiment of the present specification, L1 is a phenylene groupunsubstituted or substituted with an alkyl group; a naphthylene groupunsubstituted or substituted with an alkyl group; or a divalent fluorenegroup unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, L1 is a phenylene groupunsubstituted or substituted with an alkyl group; or a divalent fluorenegroup unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, L1 is a phenylene group;a naphthylene group; or a divalent dimethylfluorene group.

In one embodiment of the present specification, when n is 1, L3 is asubstituted or unsubstituted phenylene group.

In one embodiment of the present specification, when n is 1, L3 is aphenylene group unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, when n is 1, L3 is aphenylene group substituted with two methyl groups.

In one embodiment of the present specification, when n is 1, L3 is aphenylene group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, when n is 2, one L3 is aphenylene group, and the other L3 is an octylene group; or a hexylenegroup.

In one embodiment of the present specification, 0≤a1+a2≤2.

In one embodiment of the present specification, Chemical Formula 1 maybe represented by the following Chemical Formula 2.

In Chemical Formula 2,

L1 to L3, Ar1, Ar2, R1 to R4, r1 to r4, X1, X2, m, n, a1 and a2 have thesame definitions as in Chemical Formula 1.

In one embodiment of the present specification, the compound representedby Chemical Formula 1 is any one selected from among the followingcompounds.

The compound according to one embodiment of the present specificationmay be prepared using preparation methods to describe below. In thepreparation examples to describe below, representative examples aredescribed, however, substituents may be added or excluded as necessary,and positions of the substituents may vary. In addition, based ontechnologies known in the art, starting materials, reaction materials,reaction conditions or the like may vary.

One embodiment of the present specification provides a coatingcomposition including the compound.

According to one embodiment of the present specification, the coatingcomposition may further include a solvent.

In one embodiment of the present specification, the coating compositionmay be a liquid phase. The “liquid phase” means in a liquid state atroom temperature and atmospheric pressure.

In one embodiment of the present specification, examples of the solventmay include chlorine-based solvents such as chloroform, methylenechloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene oro-dichlorobenzene; ether-based solvents such as tetrahydrofuran ordioxane; aromatic hydrocarbon-based solvents such as toluene, xylene,trimethylbenzene or mesitylene; aliphatic hydrocarbon-based solventssuch as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane,n-octane, n-nonane or n-decane; ketone-based solvents such as acetone,methyl ethyl ketone or cyclohexanone; ester-based solvents such as ethylacetate, butyl acetate or ethyl cellosolve acetate; polyalcohols such asethylene glycol, ethylene glycol monobutyl ether, ethylene glycolmonoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane,propylene glycol, diethoxymethane, triethylene glycol monoethyl ether,glycerin or 1,2-hexanediol, and derivatives thereof; alcohol-basedsolvents such as methanol, ethanol, propanol, isopropanol orcyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide;amide-based solvents such as N-methyl-2-pyrrolidone orN,N-dimethylformamide; benzoate-based solvents such as methyl benzoate,butyl benzoate or 3-phenoxybenzoate; tetraline, and the like, however,the solvent is not limited thereto as long as it is a solvent capable ofdissolving or dispersing the compound according to one embodiment of thepresent specification.

In another embodiment, the solvent may be used either alone as one type,or as a mixture mixing two or more solvent types.

In another embodiment, the solvent preferably has a boiling point of 40°C. to 250° C. and more preferably 60° C. to 230° C., however, theboiling point is not limited thereto.

In another embodiment, viscosity of the single or mixed solvent ispreferably from 1 CP to 10 CP and more preferably from 3 CP to 8 CP, butis not limited thereto.

In another embodiment, the coating composition preferably has aconcentration of 0.1 wt/v % to 20 wt/v % and more preferably 0.5 wt/v %to 5 wt/v %, however, the concentration is not limited thereto.

In one embodiment of the present specification, the coating compositionmay further include one, two or more types of additives selected fromthe group consisting of thermal polymerization initiators andphotopolymerization initiators.

Examples of the thermal polymerization initiator may include peroxidessuch as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide,acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanoneperoxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide,bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoylperoxide, p-chlorobenzoyl peroxide, dicumyl peroxide,2,5-dimethyl-2,5-(t-butyloxy)-hexane,1,3-bis(t-butylperoxy-isopropyl)benzene, t-butyl cumyl peroxide,di-t-butyl peroxide, 2,5-dimethyl-2,5-(di-t-butylperoxy)hexane-3,tris-(t-butylperoxy)triazine,1,1-di-t-butylperoxy-3,3,5-trimethylcyclohexane,1,1-di-t-butylperoxycyclohexane, 2,2-di(t-butylperoxy)butane,4,4-di-t-butylperoxy valeric acid n-butyl ester,2,2-bis(4,4-t-butylperoxycyclohexyl)propane, t-butyl peroxyisobutyrate,di-t-butyl peroxyhexahydroterephthalate,t-butylperoxy-3,5,5-trimethylhexate, t-butyl peroxybenzoate ordi-t-butyl peroxytrimethyl adipate; or azo-based such as azobisisobutylnitrile, azobis dimethylvaleronitrile or azobis cyclohexylnitrile, but are not limited thereto.

Examples of the photopolymerization initiator may includeacetophenone-based or ketal-based photopolymerization initiators such asdiethoxyacetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one,1-hydroxy-cyclohexyl-phenyl-ketone,4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1,2-hydroxy-2-methyl-1-phenylpropan-1-one,2-methyl-2-morpholino(4-methylthiophenyl)propan-1-one or1-phenyl-1,2-propanedion-2-(o-ethoxycarbonyl)oxime; benzoin ether-basedphotopolymerization initiators such as benzoin, benzoin methyl ether,benzoin ethyl ether, benzoin isobutyl ether or benzoin isopropyl ether;benzophenone-based photopolymerization initiators such as benzophenone,4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoylbiphenyl,4-benzoyl phenyl ether, acrylated benzophenone or 1,4-benzoylbenzene;thioxanthone-based photopolymerization initiators such as2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone,2,4-diethylthioxanthone or 2,4-dichlorothioxanthone; and, as otherphotopolymerization initiators, ethyl anthraquinone,2,4,6-trimethylbenzoyldiphenylphosphine oxide,2,4,6-trimethylbenzoylphenylethoxyphosphine oxide,bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide,bis(2,4-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide,methylphenylglyoxyester, 9,10-phenanthrene, acridine-based compounds,triazine-based compounds, imidazole-based compounds, and the like, butare not limited thereto.

In addition, those having a photopolymerization facilitating effect maybe used either alone or together with the photopolymerization initiator.Examples thereof may include triethanolamine, methyldiethanolamine,ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate,(2-dimethylamino)ethyl benzoate, 4,4′-dimethylaminobenzophenone and thelike, but are not limited thereto.

Another embodiment of the present specification provides an organiclight emitting device formed using the coating composition.

In one embodiment of the present specification, the organic lightemitting device includes a first electrode; a second electrode providedopposite to the first electrode; and one or more organic material layersprovided between the first electrode and the second electrode, whereinone or more layers of the organic material layers include the coatingcomposition and a cured material thereof.

In one embodiment of the present specification, the first electrode is acathode, and the second electrode is an anode.

In another embodiment, the first electrode is an anode, and the secondelectrode is a cathode.

In one embodiment of the present specification, the organic materiallayer formed using the coating composition is a hole transfer layer, ahole injection layer, or a layer carrying out hole transfer and holeinjection at the same time.

In one embodiment of the present specification, the organic materiallayer including the coating composition or a cured material thereof is alight emitting layer.

In one embodiment of the present specification, the coating compositionmay further include an ionic compound represented by an anion grouprepresented by the following Chemical Formula 11; and a cation grouprepresented by the following Chemical Formula 12.

In Chemical Formula 11,

at least one of R101 to R120 is F; a cyano group; or a substituted orunsubstituted fluoroalkyl group,

at least one of the remaining R101 to R120 is a curing group, and

the remaining R101 to R120 are the same as or different from each other,and each independently hydrogen; deuterium; a nitro group; a substitutedor unsubstituted alkyl group; a substituted or unsubstituted alkenylgroup; a substituted or unsubstituted amine group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heterocyclicgroup,

in Chemical Formula 12,

R121 to R130 are the same as or different from each other, and eachindependently hydrogen; deuterium; a nitro group; a halogen group; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedcycloalkyl group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group, or a curing group.

In the present specification, the “curing group” may mean a reactivesubstituent crosslinking compounds by being exposed to heat and/orlight. The crosslinking may be produced by linking radicals producedwhile carbon-carbon multiple bonds or cyclic structures are decomposedby heat treatment or light irradiation.

In one embodiment of the present specification, the curing group is anyone selected from among the following structures.

In the structures,

L11 is a direct bond; —O—; —S—; a substituted or unsubstituted alkylenegroup; a substituted or unsubstituted arylene group; or a substituted orunsubstituted heteroarylene group,

k is 1 or 2,

when k is 2, L11s are the same as or different from each other, and

R131 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the curing group ofChemical Formula 11 is a vinyl group.

In one embodiment of the present specification, R103, R108, R113 andR118 of Chemical Formula 11 are the same as or different from eachother, and each independently a vinyl group or F.

In one embodiment of the present specification, at least one of R103,R108, R113 and R118 of Chemical Formula 11 is a curing group.

In one embodiment of the present specification, at least one of R103,R108, R113 and R118 of Chemical Formula 11 is a vinyl group.

In one embodiment of the present specification, at least one of R103,R108, R113 and R118 of Chemical Formula 11 is a vinyl group, and therest are F.

In one embodiment of the present specification, the anion grouprepresented by Chemical Formula 11 is any one selected from among thefollowing structures.

In one embodiment of the present specification, the cation grouprepresented by Chemical Formula 12 is any one selected from among thefollowing structures.

In one embodiment of the present specification, the organic lightemitting device may further include one, two or more layers selectedfrom the group consisting of a hole injection layer, a hole transferlayer, an electron transfer layer, an electron injection layer, anelectron injection and transfer layer, an electron blocking layer and ahole blocking layer.

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in which an anode, oneor more organic material layers and a cathode are consecutivelylaminated on a substrate (normal type).

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in a reverse directionin which a cathode, one or more organic material layers and an anode areconsecutively laminated on a substrate (inverted type).

The organic material layer of the organic light emitting device of thepresent specification may be formed in a single layer structure, but mayalso be formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice of the present specification may have a structure including ahole injection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, and may include a smaller numberof organic material layers.

For example, a structure of the organic light emitting device accordingto one embodiment of the present specification is illustrated in theFIGURE.

The FIGURE illustrates a structure of the organic light emitting devicein which an anode (201), a hole injection layer (301), a hole transferlayer (401), a light emitting layer (501), an electron injection andtransfer layer (601) and a cathode (701) are consecutively laminated ona substrate (101).

The FIGURE illustrates the organic light emitting device, however, theorganic light emitting device is not limited thereto.

When the organic light emitting device includes a plurality of organicmaterial layers, the organic material layers may be formed withmaterials that are the same as or different from each other.

The organic light emitting device of the present specification may bemanufactured using materials and methods known in the art, except thatone or more layers of the organic material layers are formed using thecoating composition.

For example, the organic light emitting device of the presentspecification may be manufactured by consecutively laminating an anode,an organic material layer and a cathode on a substrate. Herein, theorganic light emitting device may be manufactured by forming an anode ona substrate by depositing a metal, a metal oxide having conductivity, oran alloy thereof using a physical vapor deposition (PVD) method such assputtering or e-beam evaporation, forming an organic material layerincluding a hole injection layer, a hole transfer layer, a lightemitting layer and an electron transfer layer thereon, and thendepositing a material capable of being used as a cathode thereon. Inaddition to such a method, the organic light emitting device may also bemanufactured by consecutively depositing a cathode material, an organicmaterial layer and an anode material on a substrate.

Another embodiment of the present specification provides a method formanufacturing an organic light emitting device formed using the coatingcomposition.

Specifically, in one embodiment of the present specification, the methodfor manufacturing an organic light emitting device includes preparing asubstrate; forming a cathode or an anode on the substrate; forming oneor more organic material layers on the cathode or the anode; and formingan anode or a cathode on the organic material layer, wherein the formingof organic material layers includes forming one or more organic materiallayers using the coating composition.

In one embodiment of the present specification, the organic materiallayer formed using the coating composition is formed using spin coatingor inkjetting.

In another embodiment, the organic material layer formed using thecoating composition is formed using a printing method.

In an embodiment of the present specification, examples of the printingmethod include inkjet printing, nozzle printing, offset printing,transfer printing, screen printing or the like, but are not limitedthereto.

The coating composition according to one embodiment of the presentspecification is suited for a solution process due to its structuralproperties and may be formed using a printing method, and therefore, iseconomically effective in terms of time and costs when manufacturing adevice.

In one embodiment of the present specification, the forming of anorganic material layer formed using the coating composition includescoating the coating composition on the cathode or the anode; and heattreating or light treating the coated coating composition.

In one embodiment of the present specification, the time of heattreating the organic material layer formed using the coating compositionis preferably within 1 hour and more preferably within 30 minutes.

In one embodiment of the present specification, the atmosphere of heattreating the organic material layer formed using the coating compositionis preferably inert gas such as argon or nitrogen.

When the forming of organic material layers using the coatingcomposition includes the heat treating or light treating, a plurality offluorene groups included in the coating composition form crosslinking,and an organic material layer including a thin-filmed structure may beprovided. In this case, being dissolved by a solvent deposited on asurface of the organic material layer formed using the coatingcomposition, or being morphologically influenced or decomposed may beprevented.

Accordingly, when the organic material layer formed using the coatingcomposition is formed including the heat treating or light treating,resistance for a solvent increases, and a multilayer may be formed byrepeatedly performing solution deposition and crosslinking method, andas a result, lifetime properties of a device may be enhanced due toincreased stability.

In one embodiment of the present specification, the coating compositionincluding the compound may use a coating composition mixed to a polymerbinder and dispersed.

In one embodiment of the present specification, as the polymer binder,those that do not extremely inhibit charge transfer are preferred, andthose that do not have strong absorption for visible light arepreferably used. Examples of the polymer binder may includepoly(N-vinylcarbazole), polyaniline and derivatives thereof,polythiophene and derivatives thereof, poly(p-phenylenevinylene) andderivatives thereof, poly(2,5-thienylenevinylene) and derivativesthereof, polycarbonate, polyacrylate, polymethyl acrylate, polymethylmethacrylate, polystyrene, polyvinyl chloride, polysiloxane and thelike.

In addition, the compound according to one embodiment of the presentspecification may be included alone in the organic material layer, ormay be included as a copolymer using a coating composition mixed withother monomers. In addition, a copolymer or a mixture may be includedusing a coating composition mixed with other polymers.

As the anode material, materials having large work function are normallypreferred so that hole injection to an organic material layer is smooth.Specific examples of the anode material capable of being used in thepresent specification include metals such as vanadium, chromium, copper,zinc and gold, or alloys thereof; metal oxides such as zinc oxide,indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO);combinations of metals and oxides such as ZnO:Al or SnO₂:Sb; conductivepolymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole andpolyaniline, and the like, but are not limited thereto.

As the cathode material, materials having small work function arenormally preferred so that electron injection to an organic materiallayer is smooth. Specific examples of the cathode material includemetals such as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

The hole injection layer is a layer that injects holes from anelectrode, and the hole injection material is preferably a compound thathas an ability to transfer holes and thereby has a hole injection effectin an anode and an excellent hole injection effect for a light emittinglayer or a light emitting material, prevents excitons generated in thelight emitting layer from moving to an electron injection layer or anelectron injection material, and in addition thereto, has an excellentthin film forming ability. The highest occupied molecular orbital (HOMO)of the hole injection material is preferably in between the workfunction of an anode material and the HOMO of surrounding organicmaterial layers. Specific examples of the hole injection materialinclude metal porphyrins, oligothiophene, arylamine-based organicmaterials, hexanitrile hexaazatriphenylene-based organic materials,quinacridone-based organic materials, perylene-based organic materials,anthraquinone, and polyaniline- and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

The hole transfer layer is a layer that receives holes from a holeinjection layer and transfers the holes to a light emitting layer, andas the hole transfer material, materials capable of receiving holes froman anode or a hole injection layer, moving the holes to a light emittinglayer, and having high mobility for the holes are suited. Specificexamples thereof include arylamine-based organic materials, conductivepolymers, block copolymers having conjugated parts and non-conjugatedparts together, and the like, but are not limited thereto.

The light emitting material is a material capable of emitting light in avisible light region by receiving holes and electrons from a holetransfer layer and an electron transfer layer, respectively, and bindingthe holes and the electrons, and is preferably a material havingfavorable quantum efficiency for fluorescence or phosphorescence.Specific examples thereof include 8-hydroxyquinoline aluminum complexes(Alg₃); carbazole-based compounds; dimerized styryl compounds; BAlq;10-hydroxybenzoquinoline-metal compounds; benzoxazole-, benzothiazole-and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-basedpolymers; spiro compounds; polyfluorene, rubrene, or the like, but arenot limited thereto.

The light emitting layer may include a host material and a dopantmaterial. The host material includes fused aromatic ring derivatives,heteroring-containing compounds or the like. Specifically, the fusedaromatic ring derivative includes anthracene derivatives, pyrenederivatives, naphthalene derivatives, pentacene derivatives,phenanthrene compounds, fluoranthene compounds and the like, and theheteroring-containing compound includes carbazole derivatives,dibenzofuran derivatives, ladder-type furan compounds, pyrimidinederivatives and the like, however, the material is not limited thereto.

The dopant material includes aromatic amine derivatives, styrylaminecompounds, boron complexes, fluoranthene compounds, metal complexes andthe like. Specifically, the aromatic amine derivative is a fusedaromatic ring derivative having a substituted or unsubstituted arylaminegroup and includes arylamine group-including pyrene, anthracene,chrysene, peryflanthene and the like, and the styrylamine compound is acompound in which substituted or unsubstituted arylamine is substitutedwith at least one arylvinyl group, and one, two or more substituentsselected from the group consisting of an aryl group, a silyl group, analkyl group, a cycloalkyl group and an arylamine group are substitutedor unsubstituted. Specifically, styrylamine, styryldiamine,styryltriamine, styryltetramine or the like is included, however, thestyrylamine compound is not limited thereto. In addition, the metalcomplex includes iridium complexes, platinum complexes or the like, butis not limited thereto.

The electron transfer layer is a layer that receives electrons from anelectron injection layer and transfers the electrons to a light emittinglayer, and as the electron transfer material, materials capable offavorably receiving electrons from a cathode, moving the electrons to alight emitting layer, and having high mobility for the electrons aresuited. Specific examples thereof include Al complexes of8-hydroxyquinoline; complexes including Alq₃; organic radical compounds;hydroxyflavon-metal complexes, or the like, but are not limited thereto.The electron transfer layer may be used together with any desiredcathode material as used in the art. Particularly, examples of thesuitable cathode material include common materials that have small workfunction, and in which an aluminum layer or a silver layer follows.Specifically, the cathode material includes cesium, barium, calcium,ytterbium and samarium, and in each case, an aluminum layer or a silverlayer follows.

The electron injection layer is a layer that injects electrons from anelectrode, and the electron injection material is preferably a compoundthat has an ability to transfer electrons, has an electron injectioneffect from a cathode, has an excellent electron injection effect for alight emitting layer or a light emitting material, prevents excitonsgenerated in the light emitting layer from moving to a hole injectionlayer, and in addition thereto, has an excellent thin film formingability. Specific examples thereof include fluorenone,anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole,oxadiazole, triazole, imidazole, perylene tetracarboxylic acid,fluorenylidene methane, anthrone or the like, and derivatives thereof,metal complex compounds, nitrogen-containing 5-membered ringderivatives, and the like, but are not limited there.

The metal complex compound includes 8-hydroxyquinolinato lithium,bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but isnot limited thereto.

The hole blocking layer is a layer blocking holes from reaching acathode, and generally, may be formed under the same condition as thehole injection layer. Specifically, oxadiazole derivatives or triazolederivatives, phenanthroline derivatives, aluminum complexes and the likeare included, however, the material is not limited thereto.

The organic light emitting device according to the present specificationmay be a top-emission type, a bottom-emission type or a dual-emissiontype depending on the materials used.

In one embodiment of the present specification, the compound may beincluded in an organic solar cell or an organic transistor in additionto the organic light emitting device.

Hereinafter, the present specification will be described in detail withreference to examples in order to specifically describe the presentspecification. However, the examples according to the presentspecification may be modified to various different forms, and the scopeof the present specification is not to be construed as being limited tothe examples described below. Examples of the present specification areprovided in order to more fully describe the present specification tothose having average knowledge in the art.

PREPARATION EXAMPLE <Preparation Example 1-1>-Preparation of Compound 1Preparation of Intermediate I-1

To a flask holding 3-bromo-9-phenyl-9H-carbazole (16.11 g, 50.0 mmol),4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (10.95 g, 50.0mmol), tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) andK₂CO₃ (20.23 g, 100.0 mmol), THF/H₂O (v/v=3/1) (800 ml) was introduced,and the result was stirred for 16 hours at 80° C. under N₂. After thereaction was finished, the reaction solution was cooled, and then theorganic layer was extracted using an extraction flask. The organic layerwas dried with MgSO₄, the organic solvent was removed using a rotaryvacuum evaporator, and then the residue was column purified to obtainI-1 (10.2 g, yield 51%, HPLC purity 99.4%).

Preparation of Intermediate I-2

To a flask holding I-1 (3.2 g, 10.0 mmol), bromobenzene (1.57 g. 10.0mmol) and sodium tert-butoxide (2.4 g, 25.0 mmol), toluene wasintroduced. The flask holding the reaction material was placed in an 90°C. oil bath, then Pd(PtBu₃)₂ (153 mg, 0.3 mmol) was introduced thereto,and the result was stirred for 1 hour. Water was introduced thereto tostop the reaction, and after extracting the result with dichloromethane(DCM), the organic layer was dried with MgSO₄. The organic solvent wasremoved using a rotary vacuum evaporator, and then the residue wascolumn purified to obtain I-2 (2.99 g, yield 73%, HPLC purity 99.6%).

Preparation of Intermediate A-1

2-Bromo-9H-fluoren-9-one (25.9 g, 100 mmol) was dissolved in anhydroustetrahydrofuran (THF). Phenylmagnesium bromide (3 M in THF, 48 ml, 144mmol) was introduced thereto, and the result was stirred for 20 minutes.The reaction was stopped using NH₄Cl (aq), and the water layer wasseparated and then extracted with ethyl acetate (EA). The organic layerwas dried with MgSO₄, and the organic solvent was removed using a rotaryvacuum evaporator. The residue was dissolved in DCM, and afterintroducing triethylsilane (23.3 ml, 145 mmol) and trifluoroacetic acid(11.7 ml) thereto, the result was stirred overnight at room temperature(RT). The organic solvent was removed using a rotary vacuum evaporator,and the result was silica filtered. The organic solvent was removedusing a rotary vacuum evaporator again, and the result wasrecrystallized using dichloromethane and hexane to obtain A-1 (20.6 g,yield 61%).

Preparation of Intermediate A-2

A-1 (20.6 g, 61 mmol) and phenol (17.2 g, 183 mmol) were introduced anddissolved in methanesulfonic acid (82 ml, 304 mmol). A dean-starkapparatus was installed, and the result was refluxed. After that, thereaction was stopped using a saturated aqueous NaHCO₃ solution, and theorganic layer was extracted with ethyl acetate. The organic layer wasdried with MgSO₄, the solvent was removed, and the result was purifiedusing column chromatography to obtain Intermediate Compound A-2 (21 g,yield 84%).

Preparation of Intermediate A-3

A-2 (21 g, 51.0 mmol), 4-bromobenzaldehyde (11.1 g, 60 mmol) and K₂CO₃(30.4 g, 150.0 mmol) were introduced and dissolved in anhydrous pyridine(100 ml, 0.25 M). After that, copper(II) oxide (8.1 g, 100 mmol) wasslowly added thereto, and the reaction was progressed while refluxingthe result after raising the temperature to 120° C. After the reactionwas finished, the reaction was stopped using a saturated aqueous NaHCO₃solution, and the organic layer was extracted with ethyl acetate. Theorganic layer was dried with MgSO₄, and a crude obtained by removing thesolvent was dissolved in dichloromethane, and precipitated in ethanol toobtain solid Intermediate Compound A-3 (20.6 g, yield 78%).

Preparation of Intermediate A

After introducing methyltriphenylphosphonium bromide (28.58 g, 80 mmol)to anhydrous tetrahydrofuran (THF) (100 ml), the result was stirred for30 minutes at 0° C. using an ice bath, and after introducingpotassium-tert-butoxide (9.0 g, 80 mmol) thereto at once, the result wasfurther stirred for 20 minutes in an ice bath. Intermediate Compound A-3(20.6 g, 39.8 mmol) was dissolved in tetrahydrofuran (THF) (70 ml), andgradually added to the mixture using a dropping funnel. After that, theflask and the funnel were washed with THF (15 ml), and the THF was addedto the flask. The reaction was terminated by introducing water (80 ml)thereto, and the organic layer was extracted with ethyl acetate.Moisture was removed from the extracted organic layer using MgSO₄, andafter removing the organic solvent, the result was purified using columnchromatography to obtain Intermediate Compound A (19.2 g, 37.3 mmol).

Preparation of Compound 1

After introducing I-2 (2.99 g, 7.28 mmol), A (3.86 g, 7.5 mmol), NaOt-Bu(2.16 g, 22.5 mmol) and Pd(PtBu₃)₂ (112 mg, 0.22 mmol) to toluene (80ml), the result was stirred for 0.5 hours at 80° C. under the N₂atmosphere. The reaction was stopped by introducing water thereto, andafter extracting the result with diethyl ether, the organic layer wasdried with MgSO₄, the organic solvent was removed using a rotary vacuumevaporator, and then the result was purified using columnchromatography. As a result, off-white Compound 1 (4.24 g, 5.0 mmol) wasobtained. The obtained compound was identified using LCMS.

MS: 844.4

Preparation of Intermediate II-1

To a flask holding 3,6-dibromo-9-phenyl-9H-carbazole (20.05 g, 50 mmol),4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (11.60 g, 50mmol), tetrakis(triphenylphosphine) palladium (0) (1.73 g, 1.5 mmol) andK₂CO₃ (20.23 g, 100.0 mmol), THF/H₂O (v/v=3/1) (900 ml) was introduced,and the result was stirred for 5 hours at 80° C. under N₂. After thereaction was finished, the reaction solution was cooled, and then theorganic layer was extracted using an extraction flask. The organic layerwas dried with MgSO₄, the organic solvent was removed using a rotaryvacuum evaporator, and then the residue was column purified to obtainII-1 (10.0 g, yield 47%, HPLC purity 98.9%).

Preparation of Intermediate II-2

Intermediate II-2 (9.04 g, yield 90.6%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that II-1 was used instead of A-3.

Preparation of Intermediate II-3

Intermediate II-3 (6.02 g, yield 64.8%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-1 except that II-2 was used instead of3-bromo-9-phenyl-9H-carbazole.

Preparation of Intermediate II-4

Intermediate II-4 (1.78 g, yield 87.8%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-2 except that II-3 was used instead of I-1 and4-bromo-1,1′-biphenyl was used instead of bromobenzene.

Preparation of Compound 6

Compound 6 (2.79 g, yield 90.3%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofCompound 1 except that II-4 was used instead of I-2. The obtainedcompound was identified using LCMS.

MS: 1022.6

Preparation of Intermediate III-1

Intermediate III-1 (4.58 g, yield 50.8%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-1 except that 3-bromo-9-(4-vinylphenyl)-9H-carbazole wasused instead of 3-bromo-9-phenyl-9H-carbazole.

Preparation of Intermediate III-2

Intermediate III-2 (2.6 g, yield 83.2%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate II-4 except that III-1 was used instead of II-3.

Preparation of Intermediate B-1

Intermediate B-1 (9.3 g, yield 79%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-1 except that (4-(tert-butyl)phenyl)magnesium bromide wasused instead of phenylmagnesium bromide.

Preparation of Intermediate B-2

Intermediate B-2 (9.0 g, yield 81%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-2 except that B-1 was used instead of A-1.

Preparation of Intermediate B-3

Intermediate B-3 (8.15 g, yield 74%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-3 except that B-2 was used instead of A-2.

Preparation of Intermediate B

Intermediate B (7.32 g, yield 92%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that B-3 was used instead of A-3.

Preparation of Compound 14

Compound 14 (2.15 g, yield 83%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 1except that III-2 was used instead of I-2 and Intermediate B was usedinstead of Intermediate A. The obtained compound was identified usingLCMS.

MS: 1002.9

Preparation of Intermediate IV-1

Intermediate IV-1 (1.68 g, yield 87%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate II-4 except that 2-bromonaphthalene was used instead of4-bromo-1,1′-biphenyl.

Preparation of Compound 25

Compound 25 (2.65 g, yield 89%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 1except that IV-1 was used instead of I-2. The obtained compound wasidentified using LCMS.

MS: 998.2

Preparation of Intermediate V-1

Intermediate V-1 (2.44 g, yield 78%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate III-2 except that 2-bromo-1,1′-biphenyl was used instead of4-bromo-1,1′-biphenyl.

Preparation of Compound 57

Compound 57 (3.38 g, yield 71%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 14except that V-1 was used instead of III-2.

MS: 1003.6

Preparation of Intermediate VI-1

Intermediate VI-1 (1.66 g, yield 69%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate II-4 except that 4-bromo-4′-octyl-1,1′-biphenyl was usedinstead of 4-bromo-1,1′-biphenyl.

Preparation of Compound 83

Compound 83 (1.96 g, yield 73%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 1except that VI-1 was used instead of I-2.

MS: 1136.4

Preparation of Intermediate VII-1

Intermediate VII-1 (1.90 g, yield 88%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate II-4 except that 2-bromo-9,9-dimethyl-9H-fluorene was usedinstead of 4-bromo-1,1′-biphenyl.

Preparation of Compound 87

Compound 87 (2.74 g, yield 81%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 14except that VII-1 was used instead of III-2. The obtained compound wasidentified using LCMS.

MS: 1119.8

Preparation of Intermediate VIII-1

Intermediate VIII-1 (7.06 g, yield 63%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate III-1 except that 3-bromo-9-(4-vinylphenyl)-9H-carbazolewas used instead of 3,6-dibromo-9-phenyl-9H-carbazole.

Preparation of Intermediate VIII-2

Intermediate VIII-2 (6.61 g, yield 94%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that VIII-1 was used instead of A-3.

Preparation of Intermediate VIII-3

After dissolving VIII-2 (6.61 g, 17.8 mmol) in DMF (200 ml) and stirringthe result for 15 minutes at room temperature under the N₂ atmosphere,n-bromosuccinimide (3.11 g, 17.5 mmol) dissolved in DMF (50 ml) wasslowly added dropwise thereto, and the result was stirred for 16 hours.Water (250 ml) was introduced thereto to finish the reaction, anddropped precipitates were filtered and dried for 20 hours at 60° C. toobtain VIII-3 (5.54 g, 12.3 mmol) in 95% purity.

Preparation of Intermediate VIII-4

Intermediate VIII-4 (3.81 g, yield 67%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-1 except that Intermediate VIII-3 was used instead of3-bromo-9-phenyl-9H-carbazole.

Preparation of Intermediate VIII-5

Intermediate VIII-5 (4.30 g, yield 83%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-2 except that Intermediate VIII-4 was used instead ofIntermediate I-1 and 3-bromodibenzo[b,d]furan was used instead ofbromobenzene.

Preparation of Intermediate C-1

Intermediate C-1 (3.14 g, yield 86%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-1 except that (2,5-dimethylphenyl)magnesium bromide wasused instead of phenylmagnesium bromide.

Preparation of Intermediate C-2

Intermediate C-2 (3.04 g, yield 81%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-2 except that C-1 was used instead of A-1.

Preparation of Intermediate C-3

Intermediate C-3 (2.89 g, yield 77%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-3 except that C-2 was used instead of A-2.

Preparation of Intermediate C

Intermediate C (2.53 g, yield 88%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that C-3 was used instead of A-3.

Preparation of Compound 96

Compound 96 (2.91 g, yield 89%) was obtained using the same equivalents,and synthesis and purification methods as in Preparation of Compound 1except that Intermediate VIII-5 was used instead of Intermediate I-2 andIntermediate C was used instead of Intermediate A. The obtained compoundwas identified using LCMS.

MS: 1092.4

Preparation of Intermediate D-1

Intermediate D-1 (5.45 g, yield 61.7%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-2 except that 2,6-xylenol was used instead of phenol.

Preparation of Intermediate D-2

Intermediate D-2 (4.74 g, yield 70.3%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A-3 except that Intermediate D-1 was used instead ofIntermediate A-2.

Preparation of Intermediate D

Intermediate D (4.35 g, 8.0 mmol) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that Intermediate D-2 was used instead ofIntermediate A-3.

Preparation of Compound 107

Compound 107 (6.51 g, yield 77.4%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofCompound 6 except that Intermediate D was used instead of IntermediateA. The obtained compound was identified using LCMS.

MS: 1050.5

Preparation of Intermediate E-1

To a 500 mL 1-neck round bottom flask (RBF), A-1 (10 g, 29.7 mmol) wasintroduced, and dissolved by introducing dichloromethane (150 ml)thereto. Triethylsilane (7.8 ml, 50 mmol) and trifluoroacetic acid (3.5ml, 12 mmol) were added dropwise thereto, and the result was stirred for24 hours. Silica gel was dropped to adsorb the result, and the resultwas columned using hexane to obtain Intermediate E-1 (8.2 g, yield85.8%).

Preparation of Intermediate E-2

To a 250 mL 1-neck round bottom flask (RBF), E-1 (8.2 g, 25.5 mmol),4-(4-(8-bromooctyl)phenoxy)benzaldehyde (10.9 g, 28.0 mmol) andtetrabutylammonium bromide (0.64 g, 2 mmol) were introduced, anddissolved by adding toluene (100 ml) thereto. The flask was degassed forapproximately 30 minutes after raising the temperature to approximately50° C., 15 wt % NaOH (25 ml) was introduced thereto, and the result wasreacted for approximately 18 hours at 60° C. Ammonium chloride wasintroduced thereto to terminate the reaction, water was added thereto,and the organic layer was extracted using EA. The obtained organic layerwas dried with MgSO₄, concentrated, and then recrystallized usingmethylene chloride (MC) and ethanol to obtain E-2 (7.7 g, yield 48.3%).

Preparation of Intermediate E

Intermediate E (7.1 g, 11.3 mmol) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate A except that Intermediate E-2 was used instead ofIntermediate A-3.

Preparation of Intermediate IX-1

To a flask holding 3-bromo-9-phenyl-9H-carbazole (6.96 g, 20.0 mmol),2,2′-(9,9-dimethyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(10.71 g, 24.0 mmol), tetrakis(triphenylphosphine)palladium(0) (693 mg,0.6 mmol) and K₂CO₃ (10.11 g, 50.0 mmol), tetrahydrofuran (THF)/H₂O(v/v=3/1) (500 ml) was introduced, and the result was stirred for 16hours at 80° C. under N₂. After the reaction was finished, the reactionsolution was cooled, and then the organic layer was extracted using anextraction flask. The organic layer was dried with MgSO₄, the organicsolvent was removed using a rotary vacuum evaporator, and then theresidue was column purified to obtain Intermediate IX-1 (5.11 g, yield43.5%).

Preparation of Intermediate IX-2

Intermediate IX-2 (2.9 g, yield 60.4%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate III-1 except that IX-1 was used instead of3-bromo-9-phenyl-9H-carbazole and 4-bromoaniline was used instead of4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline.

Preparation of Intermediate IX-3

Intermediate IX-3 (2.84 g, yield 83.5%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate I-2 except that IX-2 was used instead of I-1 and1-bromo-4-fluorobenzene was used instead of bromobenzene.

Preparation of Compound 18

Compound 18 (4.18 g, yield 79.7%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofCompound 1 except that Intermediate IX-3 was used instead ofIntermediate I-2 and Intermediate E was used instead of Intermediate A.The obtained compound was identified using LCMS.

MS: 1193.6

Preparation of Intermediate X-1

Intermediate X-1 (4.34 g, yield 52.9%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate III-1 except that 3-bromo-9-(4-vinylphenyl)-9H-carbazolewas used instead of 3-bromo-9-phenyl-9H-carbazole and6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-amine wasused instead of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.

Preparation of Intermediate X-2

Intermediate X-2 (3.17 g, yield 59.3%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofIntermediate III-1 except that X-1 was used instead of3-bromo-9-phenyl-9H-carbazole and 4-bromoaniline was used instead of4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline.

Preparation of Compound 23

Compound 23 (4.89 g, yield 83.1%) was obtained using the sameequivalents, and synthesis and purification methods as in Preparation ofCompound 1 except that Intermediate X-2 was used instead of IntermediateI-2. The obtained compound was identified using LCMS.

MS: 939.2

EXAMPLE Example 1

A glass substrate on which indium tin oxide (ITO) was deposited as athin film to a thickness of 1,500 Å was placed in detergent-dissolveddistilled water and ultrasonic cleaned. After the ITO was cleaned for 30minutes, ultrasonic cleaning was repeated twice using distilled waterfor 10 minutes. After the cleaning with distilled water was finished,the substrate was ultrasonic cleaned with solvents of isopropyl alcoholand acetone for 30 minutes each, dried, and then transferred to a glovebox.

On the transparent ITO electrode prepared as above, a hole injectionlayer having a thickness of 300 Å was formed by spin coating a coatingcomposition mixing Compound 1 (20 mg), Chemical Formula D-1 (1 mg) andtoluene (1 mg), and the coating composition was cured for 1 hour on ahot plate in the air. After that, the result was transferred to a vacuumdeposition apparatus, and a hole transfer layer was formed on the holeinjection layer by vacuum depositing the following a-NPD.

After depositing a-NPD to a thickness of 40 nm, a light emitting layerwas formed on the hole transfer layer by vacuum depositing the followingAlq₃ to 50 nm. On the light emitting layer, BCP was vacuum deposited toa thickness of 35 nm to form an electron injection and transfer layer. Acathode was formed on the electron injection and transfer layer bydepositing LiF to a thickness of 0.5 nm and aluminum to a thickness of100 nm.

In the above-mentioned process, the deposition rates of the organicmaterials were maintained at 0.4 Å/sec to 0.7 A/sec, the depositionrates of the LiF and the aluminum of the cathode were maintained at 0.3Å/sec and 2 Å/sec, respectively, and the degree of vacuum during thedeposition was maintained at 2×10−7 torr to 3×10−5 torr.

Example 2

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 6 was used instead of Compound 1 inExample 1.

Example 3

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 14 was used instead of Compound 1 inExample 1.

Example 4

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 25 was used instead of Compound 1 inExample 1.

Example 5

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 57 was used instead of Compound 1 inExample 1.

Example 6

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 83 was used instead of Compound 1 inExample 1.

Example 7

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 87 was used instead of Compound 1 inExample 1.

Example 8

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 96 was used instead of Compound 1 inExample 1.

Example 9

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 6 was used instead of Compound 1 andChemical Formula D-2 was used instead of Chemical Formula D-1 in Example1.

Example 10

An organic light emitting device was manufactured in the same manner asin Example 9 except that Compound 57 was used instead of Compound 6 inExample 9.

Example 11

An organic light emitting device was manufactured in the same manner asin Example 9 except that Compound 83 was used instead of Compound 6 inExample 9.

Example 12

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 6 was used instead of Compound 1 andChemical Formula D-3 was used instead of Chemical Formula D-1 in Example1.

Example 13

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 14 was used instead of Compound 6 inExample 12.

Example 14

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 83 was used instead of Compound 6 inExample 12.

Example 15

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 87 was used instead of Compound 6 inExample 12.

Example 16

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 96 was used instead of Compound 6 inExample 12.

Example 17

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 107 was used instead of Compound 6 inExample 12.

Example 18

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 18 was used instead of Compound 6 inExample 12.

Example 19

An organic light emitting device was manufactured in the same manner asin Example 12 except that Compound 23 was used instead of Compound 6 inExample 12.

Comparative Example 1

An organic light emitting device was manufactured in the same manner asin Example 1 except that the following Compound V-1 was used instead ofCompound 1 in Example 1.

Comparative Example 2

An organic light emitting device was manufactured in the same manner asin Example 1 except that the following Compound V-2 was used instead ofCompound 1 in Example 1.

Comparative Example 3

An organic light emitting device was manufactured in the same manner asin Example 1 except that the following Compound V-3 was used instead ofCompound 1 in Example 1.

For each of the organic light emitting devices manufactured in Examples1 to 19 and Comparative Examples 1 to 3, driving voltage, currentefficiency, quantum efficiency (QE) and luminance values were measuredat current density of 10 mA/cm², and time taken for luminance becoming90% with respect to initial luminance (T90) was measured at currentdensity of mA/cm². The results are shown in the following Table 1.

TABLE 1 Driving Current Lifetime Voltage Efficiency QE Luminance T90 (10Device (V) (cd/A) (%) (Cd/m²) mA/cm²) Example 1 4.22 5.03 5.33 497.6745.1 Example 2 4.03 5.14 5.22 514.82 59.6 Example 3 3.99 5.08 5.07509.43 61.3 Example 4 4.10 4.75 4.86 479.85 56.8 Example 5 4.13 4.875.07 486.81 53.4 Example 6 4.33 4.92 5.38 487.32 51.6 Example 7 3.965.11 5.07 508.56 66.1 Example 8 4.11 5.09 5.27 505.61 60.7 Example 94.38 4.64 4.58 460.13 32.3 Example 10 4.41 4.72 4.63 467.70 33.6 Example11 4.69 4.83 5.01 483.14 28.4 Example 12 3.84 5.24 5.23 529.45 69.0Example 13 3.88 5.19 5.30 515.19 72.6 Example 14 4.01 4.94 5.18 489.0658.4 Example 15 3.85 5.12 5.14 510.77 76.9 Example 16 3.98 5.21 5.46517.12 69.2 Example 17 4.46 5.01 4.98 488.85 49.7 Example 18 4.98 5.395.61 556.19 16.9 Example 19 4.17 4.61 4.83 462.64 41.5 Comparative 4.384.29 4.62 438.70 24.1 Example 1 Comparative 4.43 4.18 4.48 424.54 19.4Example 2 Comparative 4.74 3.98 4.12 402.17 12.7 Example 3

From the results of Table 1, it was identified that Examples 1 to 19manufacturing an organic light emitting device using the compound of thepresent application had a lower driving voltage, and had excellentcurrent efficiency and quantum efficiency, and also had excellentlifetime properties compared to the organic light emitting devicesmanufactured in Comparative Examples 1 to 3.

The invention claimed is:
 1. A compound represented by the followingChemical Formula 1:

wherein, in Chemical Formula 1, Ar1 and Ar2 are the same as or differentfrom each other, and each independently a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heterocyclic group; R1 toR4 are the same as or different from each other, and each independentlyhydrogen; deuterium; a halogen group; a nitrile group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted aryl group; ora substituted or unsubstituted heterocyclic group; r1 to r3 are the sameas or different from each other, and each independently from 1 to 3; r4is from 1 to 4; when r1 to r4 are each 2 or greater, the two or more R1to R4 are the same as or different from each other; X1 and X2 are thesame as or different from each other, and each independently

each

means a linking site; a1 is 0 or 1, a2 is an integer of 0 to 2; when a2is 0, L2 is a substituted or unsubstituted aryl group; or a substitutedor unsubstituted aralkyl group; when a2 is 1, L2 is a direct bond; or asubstituted or unsubstituted arylene group; when a2 is 2, L2 is atrivalent substituted or unsubstituted aryl group; L1 is a substitutedor unsubstituted arylene group; m is an integer of 1 or 2, and when m is2, L1s are the same as or different from each other; n is an integer of1 or 2, and when n is 1, L3 is a substituted or unsubstituted arylenegroup, and when n is 2, L3s are the same as or different from eachother, and each independently a substituted or unsubstituted arylenegroup and a substituted or unsubstituted alkylene group; and 0≤a1+a2≤2.2. The compound of claim 1, wherein Chemical Formula 1 is represented bythe following Chemical Formula 2:

in Chemical Formula 2, L1 to L3, Ar1, Ar2, R1 to R4, r1 to r4, X1, X2,m, n, a1 and a2 have the same definitions as in Chemical Formula
 1. 3.The compound of claim 1, wherein L1 and L3 are the same as or differentfrom each other, and each independently a substituted or unsubstitutedphenylene group.
 4. The compound of claim 1, wherein Ar1 and Ar2 are thesame as or different from each other, and each independently asubstituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; a substituted or unsubstituted naphthylgroup; a substituted or unsubstituted phenanthrene group; a substitutedor unsubstituted fluorene group; a substituted or unsubstitutedspirobifluorene group; or a substituted or unsubstituted dibenzofurangroup.
 5. The compound of claim 1, wherein the compound represented byChemical Formula 1 is any one selected from among the followingcompounds:


6. A coating composition comprising the compound of claim
 1. 7. Anorganic light emitting device comprising: a first electrode; a secondelectrode provided opposite to the first electrode; and at least oneorganic material layers provided between the first electrode and thesecond electrode, wherein the at least one organic material layerincludes the coating composition of claim 6 or a cured material thereof.8. The organic light emitting device of claim 7, wherein the curedmaterial of the coating composition is in a cured state by heat treatingor light treating the coating composition.
 9. The organic light emittingdevice of claim 7, wherein the at least one organic material layerincluding the coating composition or a cured material thereof is a holetransfer layer, a hole injection layer, or a layer carrying out holetransfer and hole injection at the same time.
 10. The organic lightemitting device of claim 7, wherein the at least one organic materiallayer including the coating composition or a cured material thereof is alight emitting layer.
 11. The organic light emitting device of claim 7,wherein coating composition further includes an ionic compound includingan anion group represented by the following Chemical Formula 11; and acation group represented by the following Chemical Formula 12:

in Chemical Formula 11, at least one of R101 to R120 is F; a cyanogroup; or a substituted or unsubstituted fluoroalkyl group; at least oneof the remaining R101 to R120 is a curing group; and the remaining R101to R120 if present are the same as or different from each other, andeach independently hydrogen; deuterium; a nitro group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkenyl group;a substituted or unsubstituted amine group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heterocyclicgroup,

in Chemical Formula 12, R121 to R130 are the same as or different fromeach other, and each independently hydrogen; deuterium; a nitro group; ahalogen group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstitutedalkenyl group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group, or a curing group. 12.The organic light emitting device of claim 11, wherein at least one ofR103, R108, R113 and R118 is a curing group.
 13. The organic lightemitting device of claim 11, wherein the curing group is any oneselected from among the following structures:

in the structures, L11 is a direct bond; —O—; —S—; a substituted orunsubstituted alkylene group; a substituted or unsubstituted arylenegroup; or a substituted or unsubstituted heteroarylene group; k is 1 or2; when k is 2, L11s are the same as or different from each other; R131is a substituted or unsubstituted alkyl group; and each

means a linking site.
 14. The organic light emitting device of claim 11,wherein the anion group represented by Chemical Formula 11 is any oneselected from among the following structures:


15. The organic light emitting device of claim 11, wherein the cationgroup represented by Chemical Formula 12 is any one selected from amongthe following structures:


16. The compound of claim 1, wherein when a2 is 0, L2 is a phenyl groupunsubstituted or substituted with deuterium, a halogen group, an alkylgroup or an alkoxy group; a fluorene group unsubstituted or substitutedwith deuterium, a halogen group, an alkyl group or an alkoxy group; or abenzyl group unsubstituted or substituted with deuterium, a halogengroup, an alkyl group or an alkoxy group, when a2 is 1, L2 is a directbond; or a phenylene group, and when a2 is 2, L2 is a trivalentsubstituted or unsubstituted phenyl group.
 17. The organic lightemitting device of claim 11, wherein the curing group of ChemicalFormula 11 is a vinyl group.
 18. The organic light emitting device ofclaim 11, wherein R103, R108, R113 and R118 are the same as or differentfrom each other, and each independently a vinyl group or F.